Propylamine → 2-(Propylamino)-1-(pyridin-3-yl)ethanol

HRID 227281ノート

反応式

HRID 227281 の反応式
Br.Br[CH2:3][C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5].[Na].[BH4-].[Na+].[CH2:15]([NH2:18])[CH2:16][CH3:17]>C(O)C>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH:4]([OH:5])[CH2:3][NH:18][CH2:15][CH2:16][CH3:17])[CH:7]=1

参加物

6

反応物 4

HCID 7852PropylamineHCID 27762343-(2-Bromoacetyl)pyridine hydrobromideHCID 4311764Sodium borohydrideHCID 5360545Sodium

生成物 1

HCID 121638712-(Propylamino)-1-(pyridin-3-yl)ethanol

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
20 °C

実験手順

To 1.01 g (3.6 mmol) of 3-bromoacetylpyridine hydrobromide, prepared as described in Example 1, was added 20 ml of absolute ethanol and 0.5 g (13.2 mmol) of sodium boronhydride (NaBH4). The reaction mixture was stirred at 20° C. for 2 hours and filtered. To the filtrate containing 3-pyridyloxirane was added 0.7 ml (8.5 mmol) of n-propylamine and heated at reflux temperature of the reaction mixture for 5 hours. The reaction mixture was then evaporated to a dry residue and to it was added 20 ml of chloroform, a solid portion was filtered off, the filtrate was evaporated and an oil residue formed was purified by column chromatography on silica gel (silica gel 60, mobile phase: CHCl3:ethyl acetate=10:2). This yields 0.33 g (50%) of 1-(3-pyridyl)-2-propylaminoethanol in the form of the oil base (molecular weight: 180.25, gross formula: C10H16N2O)

後処理

  1. filtrationfiltered
  2. additionTo the filtrate containing 3-pyridyloxirane
  3. temperatureheated
  4. temperatureat reflux temperature of the reaction mixture for 5 hours
  5. customThe reaction mixture was then evaporated to a dry residue and to it
  6. additionwas added 20 ml of chloroform
  7. filtrationa solid portion was filtered off
  8. customthe filtrate was evaporated
  9. customan oil residue formed
  10. customwas purified by column chromatography on silica gel (silica gel 60, mobile phase: CHCl3:ethyl acetate=10:2)

出典と根拠

ORDレコード
ord-0b78a1d0a98643e4bcc4f27be197a0fa
出典データセット
uspto-grants-2009_07
特許番号
US07560474B2

反応ノート

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